Sodium Azide → (+/-)-2-(Azidomethyl)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan
Reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[O:17][C:16]3[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=4[CH:24]=[CH:25][C:15]=3[CH2:14]2)(=O)=O)=CC=1.[N-:26]=[N+:27]=[N-:28].[Na+]>>[N:26]([CH2:12][CH:13]1[O:17][C:16]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=3[CH:24]=[CH:25][C:15]=2[CH2:14]1)=[N+:27]=[N-:28]Participants
3
Procedure
Treatment of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate (2.05 g, 5.72 mmol) with sodium azide (0.929 g, 14.30 mmol) generally according to the procedure described for Intermediate 24 gave (±)-2-(azidomethyl)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan. Treatment of the azide with palladium on carbon (10 wt. %, 0.094 g) generally according to the procedure described for Example 2 afforded 0.917 g (67%) of (±)-1-(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp>220° C. (dec.); Anal. calcd. for C13H17NOHCl.0.1H2O: C, 64.15; H, 7.50; N, 5.75. Found: C, 64.41; H, 7.64; N, 5.67.
Sources & evidence
- ORD record
- ord-6d344fd93a10484294f5c776888d64bc
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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